Style, Like Wisdom, Gets Better With Age
Over the next few years, the oldest millennials will hit a major milestone. Welcome to
40 Is the New 40, a series of stories about—and for—a generation rethinking what it means to get older.
When I turned 39 this past March, all sorts of emotions came up for me: excitement, joy, confusion, anxiety. I was sitting on the cusp of 40, an age when I’d always assumed I’d be a published author, married with kids, living in a Brooklyn brownstone bought from the spoils of my success. But my life, while rewarding—thank God I was still kicking post-pandemic—looked so different from the image in my mind. I was mid–book proposal, in a great relationship but nowhere close to marriage; homeownership seemed far off still.
Still, I felt an enormous amount of renewed confidence. I looked—and physically felt—better than I ever had. I’d developed a sense of ease within my skin in my late 30s that had eluded me much of my life, and that has a lot to do with how my body has changed in the past few years.
Like many women, I got curvier as I got older. I looked down one day and realized I had sprouted hips, an ass, and a little more love around my abs. I wasn’t sure whether this was Covid weight or whether I was simply entering into my thick-Rihanna era, but things had certainly shifted. I jiggled softly as I walked, emitting a womanliness that excited my boyfriend and reminded me of the Southern women in my family who made the earth move as they made their way along. And despite my new shake, I felt sturdier, more powerful.
This new strength was a welcome change. In the years prior, I had felt a bit hapless after leaving a big fashion job. Without the status of an institution behind me, I was racked with self-doubt and drained of faith in myself as a writer. I struggled to gain footing as a freelancer or find a sense of purpose—or even worth. Looking back now, I can see I was playing it so small in so many ways that there was almost a physical manifestation of my shrinking spirit. I was half of the woman I now see in the mirror. When I gained the weight, I started taking up more space. I was present, I was here, and it felt good.
I wanted this new growth to be reflected in my clothing as well. Though in truth it kind of had to: none of my old clothes even fit me anymore. Despite lockdown, I began amassing bolder, statement-making fashion that I felt sent a message about where I was in life.
Though Instagram might have you thinking you need to wear the exact same dress as the youths (or that any kind of fashion is for those under 26), I was gravitating toward an entirely different pole. I found myself attracted to clothes with endurance, originality, and sex appeal: standout pieces that could go the distance more than one season and show off what Mother Nature had given me. Marni, J.W. Anderson, Christopher John Rogers, Wales Bonner, Proenza Schouler, and Loewe all began taking up residency in my closet.
I wasn’t wearing much of them beyond the living room, mind you, but I felt they were an external billboard of the internal progress I was making. I was no longer a young simp; I was older, wiser. I was writing big cover stories and clearing career-making opportunities. I was in a significant relationship and building a life with someone. I had a strong, supportive community of friends. I was coming into focus.
Of course, dressing for a new body comes with challenges. Skirts and pants, I was finding, are harder, as everything has to be altered, so I have to size up and get everything taken in by my trusted tailor. It’s tedious, but it’s the only thing that ensures a custom fit. Instead, a power move always is a one-and-done megadress. My closet is stuffed with them—as it is with swimwear.
I spent most of my 20s trying to hide my stretch marks and small chest when poolside, berating myself for not being able to fill out a string bikini with a bounty of cleavage or smooth, blemish-free skin. But one summer while sunbathing in Miami, I was turned on to the high cut of a French bikini bottom: a throwback silhouette that both lengthens and accentuates your lower half with its ultra-high-rise hip. My younger self would have balked at the amount of exposed flesh the suits demand, but the combination of sun, salt water, and age led me to an epiphany: What is it worth to be on vacation and still feel self-conscious? How is that escapism?
Letting those insecurities subside, I began to let it all hang out with a near-endless stream of barely there suits from Isa Boulder, Louisa Ballou, Attico and Miaou. Using bold, flashy prints, with bottoms cut to who-knows-where, these designers know how to create for a woman with heft and very few Fs to give.
I won’t lie, though: I still battle pangs of anxiety around my body changing right in front of me. I have to consistently challenge the sizeist mindset I was indoctrinated into by years working in fashion—not to mention the notion that you have somehow aged out of fashion relevance altogether once your late 30s/early 40s hit. There are far too many style icons to prove that a lie (Tracee Ellis Ross, Chloë Sevigny, Jane Fonda, Diane Keaton, Tilda Swinton, Michelle Obama, the list goes on and on). But in an industry that is obsessed with youth and newness, there is this tacit understanding that you’re supposed to be led out to pasture at my age to make room for the latest generation of entry-level fresh faces.
I never want to grow resentful of up-and-comers—in fact, my life’s experience has made me an auntie figure to this incoming class—but what do you do when you’re just really starting to like and enjoy who you’re becoming and you’re getting passed over for PYTs with TikToks? Our culture’s obsession with 30 Under 30 lists heightens the sense that an expiration date on success and visibility is looming just as you peak.
The truth is, though, that having years behind you allows you the perspective to know that your journey is never going to be linear. It’s a circuitous path. There are plenty of twists and turns and so much evolution in your 30s. We age, we move on to different jobs, cities, take on new responsibilities within our families and communities—but we continue to love dressing for ourselves.
Before I blew out my birthday candles this year, I caught a reflection of myself in the mirror as I headed out the door. Decked in a liquidy, daisy-printed Marni gown for an all-out affair with friends and family, I smiled and thought, “Wow, I like her.”
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